The present invention concerns agents for coloring keratinic fibers, which agents contain specific m-phenylenediamine derivatives; a method for coloring hair using those agents; and certain of those m-phenylenediamine derivatives themselves and intermediate products that occur during the manufacture of those compounds.
Because of their intense colors and good fastness properties, the so-called oxidative coloring agents play a preferred role in the coloring of keratinic fibers, in particular human hair. Such coloring agents contain oxidative coloring agent precursor products, so-called developer components and coupler components. The developer components, among themselves or by coupling with one or more coupler components, form the actual dyes under the influence of oxidizing agents or atmospheric oxygen.
The developer components utilized are usually primary aromatic amines having a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives, and 2,4,5,6-tetraaminopyrimidine and its derivatives.
Specific representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl) ethanol, 2-(2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-aminopyrazolone-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxy4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino4-hydroxypyrimidine, and 1,3-N,N′-bis(2-hydroxyethyl)-N,N′-bis(4-aminophenyl)diaminopropan-2-ol.
As a rule, m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, and m-aminophenols are used as coupler components. Particularly suitable as coupler substances are 1-naphthol, 1,5-, 2,7-, and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methypyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis(2,4-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, and 2-methyl-4-chloro-5-aminophenol.
Good oxidative dye precursor products should primarily meet the following requirements: During oxidative coupling, they must form the desired color tints with sufficient intensity and fastness. They must moreover possess a good ability to absorb onto the fibers; in the case of human hair in particular, there must be no perceptible differences between grown-out and newly-grown hair (equalization capability). They should be resistant to light, heat, perspiration, abrasion, and the influence of chemical reducing agents, e.g. permanent-wave fluids. Lastly, if they are to be used as hair coloring agents, they should not impart too much color to the scalp, and most of all they need to be harmless from a toxicological and dermatological standpoint. In addition, it should be possible to easily remove from the hair, by bleaching, the coloring that is achieved, if it does not meet the particular needs of the individual person and needs to be reversed.
It is generally not possible to achieve a color tint that looks natural on the hair using only one developer component or one specific coupler/developer combination. In practice, therefore, combinations of different developer and/or coupler components are usually used. There is therefore a continual need for new, improved dye components that are also unproblematic in terms of toxicology and dermatology.